Trifluridine

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Cat Number

API0231581

CAS Number

70-00-8

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Product Detail Description Scientific Support Customer Q&A

CAS Number

70-00-8

EINECS

200-722-8

Storage

Store at 2-8℃

Synonyms

Viroptic; Trifluoromethyldeoxyuridine; Trifluridina; F3TDR; Trifluridinum; 5-(Trifluoromethyl)deoxyuridine; TFDU; 5-Trifluoromethyl-2-deoxyuridine

Molecular Formula

C10H11F3N2O5

Molecular Weight

296.2

Smiles

C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O

Appearance

White crystalline powder

Melting Point

190-193℃

Relative Density

1.4365

General Description

Trifluridine is a fluorinated pyrimidine nucleoside analogue with potent antiviral activity, formulated exclusively as a topical ophthalmic solution. It is structurally related to thymidine and acts as a DNA synthesis inhibitor. The drug is approved for the treatment of keratitis caused by herpes simplex virus and is considered the most efficacious topical agent for this indication.

Mechanism of Action

After penetrating infected corneal epithelial cells, trifluridine is phosphorylated intracellularly to the active triphosphate form. This metabolite competitively inhibits viral DNA polymerase and incorporates into viral DNA, where it causes faulty base pairing and chain termination. Viral DNA synthesis is preferentially inhibited over host DNA due to higher affinity for the viral enzyme, although some cytotoxicity to host cells occurs.

Application

Trifluridine ophthalmic solution is indicated for the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis caused by herpes simplex virus types 1 and 2. It is typically applied five times daily until corneal re-epithelialization occurs. Compared to idoxuridine and vidarabine, trifluridine demonstrates superior efficacy and lower toxicity.

Patients with metastatic colorectal cancer (mCRC) refractory to standard agents now have the oral nucleoside antitumor agent trifluridine/tipiracil (TAS‑102) as an option, but objective responses are rare and toxicities common. Ongoing efforts focus on combining TAS‑102 with anti‑angiogenic agents to improve efficacy. Certain subpopulations—those with underlying DNA repair defects or who develop neutropenia—appear to benefit more. This review covers the clinical role of TAS‑102 in mCRC, potential predictive biomarkers, and future directions.

Fig. 1 Mechanism of action of TAS-102. (Puthiamadathil JM, et al., 2017)

References

Puthiamadathil JM, Weinberg BA. Emerging combination therapies for metastatic colorectal cancer - impact of trifluridine/tipiracil. Cancer Manag Res. 2017;9:461-469.

Does Trifluridine require protection from light during storage?

Yes, it is highly photosensitive. Exposure to light causes rapid photodegradation and formation of uracil derivatives. Store in light-resistant, opaque containers.

What is the recommended storage temperature for Trifluridine?

Store at 2-8°C (refrigerated). It is thermally labile; at room temperature, dehalogenation and other degradation pathways accelerate significantly.

Is Trifluridine stable in ophthalmic solution formulations?

Formulated solutions require protection from light and refrigeration. We provide in-use stability data for ophthalmic presentations, typically stable for 30 days after opening when refrigerated.

How is the impurity 5-trifluoromethyluracil monitored during stability?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits.